Tetrahedron p. 3977 - 3982 (1992)
Update date:2022-08-03
Topics: Yield Catalyst Solvent Ambient temperature Reduction Imine one-pot synthesis Purification Workup Reaction Monitoring Stoichiometry Inert atmosphere Cyanohydrin Reaction intermediate
Zandbergen, Peter
Van Den Niewendijk, Adrianus M. C. H.
Brussee, Johannes
Van Der Gen, Arne
Kruse, Chris G.
An efficient (74% - 97% yield) three-step one-pot synthesis of (R)-Halostachine and analogues from O-protected optically active cyanohydrins is described. The reaction sequence involves a DIBAL reduction of the nitrile to an imine, transimination to a secondary imine and sodium borohydride reduction to the corresponding N-substituted β-ethanolamine. Both O-protected as well as unprotected reaction products can be obtained.
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Doi:10.1021/ic5025586
(2014)Doi:10.14233/ajchem.2013.13252
(2013)Doi:10.1134/S1070428016070265
()Doi:10.1021/jm400807n
(2013)Doi:10.1016/S0008-6215(00)90560-3
(1992)Doi:10.1055/s-0032-1317532
(2012)
